When it comes to gambling, Pokemon, and life in general, Chip will do anything he can to avoid catching the eye of fortune's fickle nature.
Between his reputation is a master gambler and the fact that he's best friend with the most famous bartender in Johto, most people assume that Chip is something of a wild card. These people couldn't be further from the truth. While certainly charming, Chip's a bit more restrained than his reputation might indicate. Gamblers who make a living off their craft aren't careless, and they aren't stupid. Like many of the greats which he strives to imitate, Chip enjoys the puzzle of discovering exactly how much he can push any given situation, and he relishes the art of outmaneuvering an opponent, whether it be a trainer, a game of cards, or one of the million curveballs life throws at aspiring trainers. Of course, get a few of Dale's drinks in him, and Chip is quick to take risks that he might normally avoid.
Competitiveness is in Chip's blood, and, despite being a gym leader, he doesn't like to pull his punches. He'll manipulate the situation to look to be disadvantageous for him only to reveal all the ways in which he actually has the upper hand. Half the reason he chose to work solely with unsolved Pokemon - other than their ability to fight in crowded spaces without harming patrons - was to create an air of weakness that he could use to make him seem weaker than he actually is. The smart trainers seeking a Vice Badge will head upstairs to challenge Dale, and Chip sees no reason to take it easy on those who are too overconfident to think that a Gym Leader using Pokemon like Voltorb couldn't be difficult to tackle. As such, Chip's battles tend to be quick and decisive.
Of course, the Gym Leader isn't a malicious person. He cares for his Pokemon deeply, and his dealers are like a family to him. He also happens to be a stubborn person who is one of the worst sore losers you'll ever meet. He still refuses to admit the name of the gym is the Goldenrod Bar and Casino despite widespread popularity, and he continues to put the casino portion of the name first. In a way, he's even more immature than his constantly buzzed best friend.
Chip spent most of his childhood with his close friend and fellow troublemaker Dale in Johto's largest metropolis: Goldenrod City. He was a smart kid, especially in whenever somebody put a puzzle in front of him, but his parents quickly grew exasperated by how inseparable he and Dale Ticker became as children. The two were constantly getting into trouble, some for good reasons, some for stupid reasons, and mostly for no real reason at all. However, when Chip's allowance finally got cut off, he began to channel his energies (and Dale's when he could) into using their mischief-making skills to make a bit of money. His proudest moment from his years of Goldenrod was dominating the Fantasy Pokemon Champion Leagues at his school. He spent entirely too much time keeping track of his spreadsheets with listing of every major trainer in the region, but he made a killing from the wealthy kids who just chose the Pokemon their favorite trainers used. Suckers.
Sadly, Chip found himself uprooted and taken to Celadon City, halfway across the world, at the impressionable age of 16. His father had gotten a gig with Silph Company's main office, and his parents didn't trust him to stay and not get arrested. Dale was just a phone-call away, but when he discovered the wonders of the Game Corner, he quickly lost his homesickness. He was savvy enough to nab a fake ID, and he found himself playing cards, rolling dice, and betting on matches almost every day after school. He quickly learned that you played the person just as much as you played the game, and he loved the thrill of outsmarting opponents and making a bit of extra cash. When he got his first Pokemon (the Voltorb which was supposed to be named Nova, but which quickly got dubbed Roulette as a parting jab at his father), he found that there was a lot more money battling and betting on yourself than just betting … if you were good. And so Chip set his mind to learning how to battle. To him, it was just like any other game in that wondrous building that was the Celadon Game Corner. The others had been easy to master, so he figured battling couldn't be much harder.
He couldn't have been more wrong. When the dealers finally caught on that he was counting cards, Chip found himself in a back alleyway being kicked by Machop commanded by men in Rocket Uniforms. He'd lost easily, and, even worse, he realized that the only part of Celadon City that made him happy was run by a gang of criminals. Wisely, Chip left the city, travelling the region, collecting badges, and learning to battle with the same mindset he brought to the gambling table. He even convinced Dale to come over to Kanto every once in a while, which led to an unforgettable night on Cinnibar with flaming shots in a bar underneath the volcano. He even helped Dale when his bar was destroyed, keeping his friend from doing something he truly regretted.
That trip to Mahogany Town got Chip thinking about his future. He'd always wanted to build his own casino, but Rocket stopped every effort in its tracks: they didn't want competition with their Celadon establishment. Between that and a conversation with Lt. Surge about training Electric Type Pokemon as a Gym Leader, Chip took the train back to his hometown in Johto, determined to make a name for himself in a place he hoped Rocket wouldn't be able to interfere. With Surge's recommendation, the League was happy to issue him a license contingent on establishing a location, and Chip settled on an abandoned warehouse in the busy nightlife scene of Goldenrod's Power and Lights district. After a bidding war led him to realize he and his old friend Dale were in it for the same reasons, the two friends combined forces once more. Their Dynamic Duo was back and better than ever.
The Goldenrod Casino and Bar is a bit of a hodgepodge between Chip and Dale's needs. The upstairs bar is a bit rustic, but Chip's casino, which dominates the first level, is a sprawling mass of flashing lights, festive music, and smartly dressed dealers and waiters. The casino has all the best games, from poker to craps to roulette to row upon row of slot machines. Heck, there's even a few tables of Voltorb Flip. The deluxe private rooms for super high rollers are upstairs, and Dale's more mainstream bartenders work on the first floor. Even aside from their status as a Pokemon Gym, Chip runs the building in a way that has earned the two a steady profit, which all employees get a cut of.
Chip's formal Gym is run in the Pokemon Battling portion of the casino. It combines a sports bar where bets are placed on high profile matches screened on televisions with the world's premier Fantasy Pokemon League, which boasts an impressive online following in Kanto and Johto. The main show however, are the live battles. There are a few arenas, most of which are relatively plain, where trainers can try and make a bit of cash battling against other patrons while onlookers place bets with a few overenthusiastic announcers. Every time Chip battles a challenger it occurs here, and most of the casino comes to watch the spectacle. Chip is nothing if not a flashy battler despite his small Pokemon.
Within the city, the Goldenrod Bar is extremely popular. Chip makes an effort to cultivate a vibrant environment and refuses to allow those addicted to gambling ruin their lives at his tables. The locale has quickly become one of the pulses of the city, right alongside the Radio Tower and the Mall, and Chip couldn't be happier.
When challengers earn the right to go up against Chip, the battle is fairly straightforward. In order to avoid appearing to favor himself, the field is bare of any terrain that would appear to give him an advantage. Of course, such field fits his style of battling perfectly, but he doesn't mention that. However, trainers must first earn 100 tokens from his casino before they can challenge him in the first place. Some with dumb luck manage to make it far enough to challenge Chip, but most without a head on their shoulders lose more money than they earn, weeding out enough that Chip isn't wasting his time on trainers without brains.
Should they emerge victorious against Chip, aspiring trainers leave with the Vice Badge, a TM of Volt Switch, and a hefty bag of tokens they can spend at the Prize Counter to buy any but the most expensive items that Chip keeps in stock.
Perhaps because he handles most of the paperwork involved in running a Gym and is generally seen as a generally responsible human being, the League tends to be a bit more patient with Chip Of course, they still hate the fact that his gym is half casino and half bar … but they also haven't revoked his license yet, which Chip counts as a win. Some of the other Gym Leaders, particularly the older ones, don't see Chip and Dale's establishment as a real Gym, and act more like it's Saffron City's Fighting Dojo, where it's more a side attraction than a 'real' Gym. Whitney in particular hates the corrupting influence of the GBC, and especially hates that, while her Gym is far more respected, the GBC is far, far more popular. A place to casually drink, gamble, and battle Pokemon? What could be better than that?
Of course, not all the Gym Leaders are prudes that hate the Gym. Lt. Surge visits often to check on his Protege, and Wattson enjoys both Chip and Dale's company immensely and visits often. Fantina has tried more than once to convince Chip to expand his outfit to include a Contest Hall. And when Grimsley heard that there was a casino that was officially affiliated with the Pokemon League, he took the first boat from Unova. It wasn't difficult to get the master gambler and Dark Type virtuoso of Unova's Elite 4 to stay for a while, and the Poker matches between he and Chip remain the stuff of legends among gambling circles.
Roulette: A gift from Chip's father in the hope that becoming a trainer would curb his son's gambling habits, Roulette had the opposite effect on Chip. For a Pokemon constructed inside Silph Labs, Roulette is unusually gleeful in battle. The more electricity he can blast out of his body, the more enjoyable it is for him. While reading nonverbals on an orb is difficult at the best of times, Chip and Roulette clearly have each other's backs. It's a rare day when Chip isn't accompanied by the Voltorb, and they both know that when things truly get hairy, Roulette's habit of blowing himself up can usually take out whomever is attacking them. The attack is so legendary that Chip has decided to give it and another unconventional attack the same name: Russian Roulette. Even when Chip calls out the order, he can never be totally sure which attack the Voltorb will use …
Slots: Slots was Lt. Surge's gift to Chip after Chip took a mentorship under the Gym Leader and was instrumental for Chip's acceptance as a Gym Leader. Like many of Surge's Pokemon, Slots is a bit stoic, displaying little emotion in favor of a militaristic silence. Even in battle, Slots acts with a precision that mimics the machinery he's named after. His magnetic manipulation abilities have helped catch more than a few cheaters who bring lead-loaded dice into GCB. Those who do are often in for a shocking surprise.
BlackJack: Chip won BlackJack by cashing in nearly all the coins he'd earned at the Celadon Game Corner to nab an egg from the far-off region of Unova. He quickly became a staple of Chip's team, as his flashy battle style and unassuming appearance fit Chip's style nicely. A go-to for opening the battle, BlackJack has a habit of hitting first and asking questions later. The Mienfoo's bravado only grew when Chip slowly exposed him to enough Electricity to shift the Pokemon's appearance and type. Now with jet black fur instead of salmon, blue lines of electricity snake their way along his paws in a fearsome display of power.